1493. Buphanitine
Nomenclature
CAS number: 4673-18-1
(1α,3α)-7-Methoxycrinan-1,3-diol; hemanthine; nerbowdine. C17H21NO5; mol wt 319.35.
C 63.94%, H 6.63%, N 4.39%, O 25.05%.
Description and references
Major alkaloid from Buphane (Bo"ophane) disticha Herb., Appleg. (Haemanthus toxicarius Herb.), Amaryllidaceae. Isoln: Lewin, Arch. Exp. Pathol. Pharmakol. 68, 333 (1912); Tutin, ibid. 69, 314 (1912). Identity with hemanthine: Goosen, Warren, Chem. Ind. 1957, 267; with nerbowdine: Lyle et al., J. Am. Chem. Soc. 82, 2620 (1960). Structure studies: Goosen, Warren, J. Chem. Soc. 1960, 1097; Goosen et al., ibid. 1961, 4038. High-resolution mass spectrum: P. Longevialle et al., Org. Mass Spectrom. 7, 401 (1973).
Properties
Needles from chloroform + ether (changes crystalline form at 210°), mp 232°. Prisms from acetone. [α]D20 -102° (c = 1 in chloroform).Derivative
Hydrochloride.C17H22ClNO5; mol wt 355.81.
C 57.39%, H 6.23%, Cl 9.96%, N 3.94%, O 22.48%.
Properties
mp 265°.Derivative
Nitrate.C17H22N2O8; mol wt 382.37.
C 53.40%, H 5.80%, N 7.33%, O 33.47%.